Please use this identifier to cite or link to this item: https://doi.org/10.1021/cs300804v
Title: Enantioselective hydrolysis of racemic and meso -epoxides with recombinant escherichia coli expressing epoxide hydrolase from Sphingomonas sp. HXN-200: Preparation of epoxides and vicinal diols in high ee and high concentration
Authors: Wu, S.
Li, A. 
Chin, Y.S.
Li, Z. 
Keywords: biocatalysis
enantioselective hydrolysis
epoxide
epoxide hydrolase
high product concentration
vicinal diol
whole-cell biotransformation
Issue Date: 5-Apr-2013
Citation: Wu, S., Li, A., Chin, Y.S., Li, Z. (2013-04-05). Enantioselective hydrolysis of racemic and meso -epoxides with recombinant escherichia coli expressing epoxide hydrolase from Sphingomonas sp. HXN-200: Preparation of epoxides and vicinal diols in high ee and high concentration. ACS Catalysis 3 (4) : 752-759. ScholarBank@NUS Repository. https://doi.org/10.1021/cs300804v
Abstract: A unique epoxide hydrolase (SpEH) from Sphingomonas sp. HXN-200 was identified and cloned based on genome sequencing and expressed in Escherichia coli. The engineered E. coli (SpEH) showed the same selectivity and substrate specificity as the wild type strain and 172 times higher activity than Sphingomonas sp. HXN-200 for the hydrolysis of styrene oxide 1. Hydrolysis of racemic styrene oxide 1, substituted styrene oxides 3, 5-7, and N-phenoxycarbonyl-3,4-epoxypiperidine 8 (200-100 mM) with resting cells of E. coli (SpEH) gave (S)-epoxides 1, 3, 5-7 and (-)-8 in 98.0-99.5% enantiomeric excess (ee) and 37.6-46.5% yield. Hydrolysis of cyclopentene oxide 9, cyclohexene oxide 10, and N-benzyloxycarbonyl-3,4-epoxypyrrolidine 11 (100 mM) afforded the corresponding (R, R)-vicinal trans-diols 12-14 in 86-93% ee and 90-99% yield. The ee of (1R, 2R)-cyclohexane-1,2-diol 13 was improved to 99% by simple crystallization. These biotransformations showed high specific activity (0.28-4.3 U/mg cdw), product concentration, product/cells ratio, and cell-based productivity. Hydrolysis at even higher substrate concentration was also achieved: (S)-1 was obtained in 430 mM (51 g/Lorg) and 43% yield; (1R, 2R)-13 was obtained in 500 mM (58 g/L) and >99% yield. Gram-scale preparation of epoxides (S)-1, (S)-3, (S)-6 and diols (1R, 2R)-12, (1R, 2R)-13, (3R, 4R)-14 were also demonstrated. E. coli (SpEH) cells showed the highest enantioselectivity to produce (S)-1 (E of 39) among all known EHs in the form of whole cells or free enzymes and the highest enantioselectivities to produce (S)-3, 5, 6, 7, (-)-8, and (R, R)-14 (E of 36, 35, 28, 57, 22, and 28) among all known EHs. The easily available and highly active E. coli (SpEH) cells are the best biocatalysts known thus far for the practical preparation of these useful and valuable enantiopure epoxides and vicinal diols via hydrolysis. © 2013 American Chemical Society.
Source Title: ACS Catalysis
URI: http://scholarbank.nus.edu.sg/handle/10635/88834
ISSN: 21555435
DOI: 10.1021/cs300804v
Appears in Collections:Staff Publications

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